# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_PH27913
_database_code_depnum_ccdc_archive 'CCDC 1552417'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Cl2 F6 Fe N4 O6 S6'
_chemical_formula_weight         883.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5957(18)
_cell_length_b                   27.983(4)
_cell_length_c                   12.851(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.958(4)
_cell_angle_gamma                90
_cell_volume                     3508.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.08

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   .930
_exptl_transmission_factor_max   .970
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.015
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37048
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.455
_diffrn_reflns_theta_max         24.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             5565
_reflns_number_gt                4499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+5.3281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5565
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.23323(5) 0.24032(2) 0.34041(4) 0.01528(13) Uani 1 1 d . . . . .
S1 S 0.23019(9) 0.20129(3) 0.17858(7) 0.0184(2) Uani 1 1 d . . . . .
S2 S 0.15729(9) 0.31939(3) 0.32144(7) 0.0184(2) Uani 1 1 d . . . . .
S3 S 0.46827(9) 0.22794(3) 0.44083(7) 0.0223(2) Uani 1 1 d . . . . .
S4 S 0.08691(9) 0.20489(3) 0.41373(7) 0.0200(2) Uani 1 1 d . . . . .
N1 N 0.0427(3) 0.14813(10) 0.0262(2) 0.0176(7) Uani 1 1 d . . . . .
N2 N 0.3264(3) 0.39200(9) 0.3407(2) 0.0186(7) Uani 1 1 d . . . . .
N3 N 0.6513(3) 0.23870(10) 0.6496(2) 0.0193(6) Uani 1 1 d . . . . .
N4 N 0.0623(3) 0.11920(10) 0.4893(2) 0.0203(7) Uani 1 1 d . . . . .
C1 C 0.0630(3) 0.18765(11) 0.0919(3) 0.0152(7) Uani 1 1 d . . . . .
C2 C -0.0544(3) 0.21452(12) 0.0783(3) 0.0196(8) Uani 1 1 d . . . . .
H2 H -0.0467 0.2420 0.1211 0.024 Uiso 1 1 calc R U . . .
C3 C -0.1811(4) 0.20016(13) 0.0016(3) 0.0271(9) Uani 1 1 d . . . . .
H3 H -0.2583 0.2181 -0.0068 0.032 Uiso 1 1 calc R U . . .
C4 C -0.1950(4) 0.15924(13) -0.0634(3) 0.0262(9) Uani 1 1 d . . . . .
H4 H -0.2807 0.1495 -0.1145 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0803(4) 0.13370(12) -0.0504(3) 0.0228(8) Uani 1 1 d . . . . .
H5 H -0.0865 0.1066 -0.0939 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2785(3) 0.34983(11) 0.2871(3) 0.0154(7) Uani 1 1 d . . . . .
C7 C 0.3312(3) 0.33539(11) 0.2077(3) 0.0187(8) Uani 1 1 d . . . . .
H7 H 0.3023 0.3067 0.1692 0.022 Uiso 1 1 calc R U . . .
C8 C 0.4246(3) 0.36310(12) 0.1864(3) 0.0212(8) Uani 1 1 d . . . . .
H8 H 0.4580 0.3531 0.1330 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4708(4) 0.40618(12) 0.2438(3) 0.0247(8) Uani 1 1 d . . . . .
H9 H 0.5346 0.4249 0.2294 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4197(4) 0.41993(11) 0.3212(3) 0.0232(8) Uani 1 1 d . . . . .
H10 H 0.4486 0.4484 0.3607 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5376(3) 0.25836(11) 0.5685(3) 0.0151(7) Uani 1 1 d . . . . .
C12 C 0.4934(3) 0.30208(11) 0.5950(3) 0.0180(8) Uani 1 1 d . . . . .
H12 H 0.4160 0.3168 0.5427 0.022 Uiso 1 1 calc R U . . .
C13 C 0.5640(4) 0.32349(12) 0.6981(3) 0.0229(8) Uani 1 1 d . . . . .
H13 H 0.5323 0.3521 0.7158 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6831(4) 0.30247(12) 0.7765(3) 0.0228(8) Uani 1 1 d . . . . .
H14 H 0.7326 0.3174 0.8451 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7248(4) 0.25981(12) 0.7502(3) 0.0230(8) Uani 1 1 d . . . . .
H15 H 0.8034 0.2451 0.8011 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1248(3) 0.14430(11) 0.4330(3) 0.0165(7) Uani 1 1 d . . . . .
C17 C 0.2155(4) 0.11855(11) 0.3979(3) 0.0201(8) Uani 1 1 d . . . . .
H17 H 0.2606 0.1341 0.3584 0.024 Uiso 1 1 calc R U . . .
C18 C 0.2382(4) 0.07060(11) 0.4215(3) 0.0251(8) Uani 1 1 d . . . . .
H18 H 0.2982 0.0539 0.3979 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1711(4) 0.04688(12) 0.4810(3) 0.0285(9) Uani 1 1 d . . . . .
H19 H 0.1864 0.0145 0.4976 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0833(4) 0.07188(12) 0.5139(3) 0.0254(8) Uani 1 1 d . . . . .
H20 H 0.0376 0.0566 0.5533 0.031 Uiso 1 1 calc R U . . .
S9 S 0.33881(9) 0.05075(3) 0.11000(7) 0.0183(2) Uani 1 1 d . . . . .
F1 F 0.1168(2) 0.03989(8) 0.14989(18) 0.0379(6) Uani 1 1 d . . . . .
F2 F 0.2659(2) -0.01637(8) 0.2167(2) 0.0483(6) Uani 1 1 d . . . . .
F3 F 0.1425(2) -0.01308(8) 0.0381(2) 0.0447(6) Uani 1 1 d . . . . .
O1 O 0.2557(3) 0.08556(8) 0.02585(19) 0.0258(6) Uani 1 1 d . . . . .
O2 O 0.4134(3) 0.07025(9) 0.2201(2) 0.0371(7) Uani 1 1 d . . . . .
O3 O 0.4133(2) 0.01878(8) 0.0670(2) 0.0282(6) Uani 1 1 d . . . . .
C21 C 0.2090(4) 0.01337(12) 0.1294(3) 0.0260(9) Uani 1 1 d . . . . .
S10 S 0.80149(9) 0.12007(3) 0.60880(7) 0.0184(2) Uani 1 1 d . . . . .
F4 F 0.5623(2) 0.11563(7) 0.43781(16) 0.0331(5) Uani 1 1 d . . . . .
F5 F 0.6178(2) 0.05126(7) 0.53808(18) 0.0386(6) Uani 1 1 d . . . . .
F6 F 0.7162(2) 0.06854(7) 0.42406(16) 0.0346(5) Uani 1 1 d . . . . .
O4 O 0.7299(2) 0.14131(8) 0.67274(18) 0.0233(6) Uani 1 1 d . . . . .
O5 O 0.8458(2) 0.15503(8) 0.54607(18) 0.0245(6) Uani 1 1 d . . . . .
O6 O 0.9006(2) 0.08373(8) 0.66609(19) 0.0269(6) Uani 1 1 d . . . . .
C22 C 0.6669(4) 0.08740(12) 0.4964(3) 0.0233(8) Uani 1 1 d . . . . .
Cl1 Cl 0.86770(10) -0.00344(3) 0.23584(8) 0.0365(2) Uani 1 1 d . . . . .
Cl2 Cl 0.84079(12) 0.09964(3) 0.19865(9) 0.0408(3) Uani 1 1 d . . . . .
C23 C 0.7523(4) 0.04423(13) 0.1769(3) 0.0337(9) Uani 1 1 d . . . . .
H23A H 0.6857 0.0453 0.2114 0.040 Uiso 1 1 calc R U . . .
H23B H 0.7033 0.0389 0.0965 0.040 Uiso 1 1 calc R U . . .
H1A H 0.109(4) 0.1319(12) 0.032(3) 0.020(11) Uiso 1 1 d . . . . .
H2A H 0.298(4) 0.4020(12) 0.385(3) 0.018(10) Uiso 1 1 d . . . . .
H3A H 0.670(4) 0.2087(13) 0.635(3) 0.031(11) Uiso 1 1 d . . . . .
H4A H 0.016(4) 0.1327(11) 0.515(3) 0.012(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 S4 2.3268(10) . ?
Fe1 S2 2.3345(9) . ?
Fe1 S1 2.3380(9) . ?
Fe1 S3 2.3410(10) . ?
S1 C1 1.728(3) . ?
S2 C6 1.736(3) . ?
S3 C11 1.737(3) . ?
S4 C16 1.738(3) . ?
N1 C5 1.353(4) . ?
N1 C1 1.356(4) . ?
N1 H1A 0.81(4) . ?
N2 C10 1.358(4) . ?
N2 C6 1.360(4) . ?
N2 H2A 0.80(3) . ?
N3 C15 1.357(4) . ?
N3 C11 1.364(4) . ?
N3 H3A 0.90(4) . ?
N4 C16 1.353(4) . ?
N4 C20 1.359(4) . ?
N4 H4A 0.78(3) . ?
C1 C2 1.405(5) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.400(4) . ?
C7 C8 1.367(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.398(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.408(5) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.357(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
S9 O2 1.432(2) . ?
S9 O3 1.438(2) . ?
S9 O1 1.467(2) . ?
S9 C21 1.821(4) . ?
F1 C21 1.332(4) . ?
F2 C21 1.337(4) . ?
F3 C21 1.333(4) . ?
S10 O6 1.441(2) . ?
S10 O4 1.446(2) . ?
S10 O5 1.457(2) . ?
S10 C22 1.830(4) . ?
F4 C22 1.330(4) . ?
F5 C22 1.340(4) . ?
F6 C22 1.340(4) . ?
Cl1 C23 1.768(4) . ?
Cl2 C23 1.777(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S4 Fe1 S2 100.90(3) . . ?
S4 Fe1 S1 112.40(3) . . ?
S2 Fe1 S1 117.73(3) . . ?
S4 Fe1 S3 116.57(4) . . ?
S2 Fe1 S3 116.56(3) . . ?
S1 Fe1 S3 93.66(3) . . ?
C1 S1 Fe1 109.37(11) . . ?
C6 S2 Fe1 103.45(11) . . ?
C11 S3 Fe1 114.53(11) . . ?
C16 S4 Fe1 108.65(11) . . ?
C5 N1 C1 124.8(3) . . ?
C5 N1 H1A 117(2) . . ?
C1 N1 H1A 119(2) . . ?
C10 N2 C6 124.1(3) . . ?
C10 N2 H2A 116(2) . . ?
C6 N2 H2A 120(2) . . ?
C15 N3 C11 124.0(3) . . ?
C15 N3 H3A 121(2) . . ?
C11 N3 H3A 115(2) . . ?
C16 N4 C20 124.0(3) . . ?
C16 N4 H4A 119(2) . . ?
C20 N4 H4A 117(2) . . ?
N1 C1 C2 116.2(3) . . ?
N1 C1 S1 117.1(2) . . ?
C2 C1 S1 126.7(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 119.5(3) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N2 C6 C7 116.3(3) . . ?
N2 C6 S2 117.7(2) . . ?
C7 C6 S2 126.0(2) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N2 C10 C9 119.8(3) . . ?
N2 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N3 C11 C12 116.6(3) . . ?
N3 C11 S3 116.5(2) . . ?
C12 C11 S3 126.9(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N3 C15 C14 119.8(3) . . ?
N3 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N4 C16 C17 116.3(3) . . ?
N4 C16 S4 116.6(2) . . ?
C17 C16 S4 127.1(2) . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 118.8(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 N4 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
N4 C20 H20 120.0 . . ?
O2 S9 O3 116.25(16) . . ?
O2 S9 O1 114.62(15) . . ?
O3 S9 O1 113.07(14) . . ?
O2 S9 C21 103.79(16) . . ?
O3 S9 C21 104.62(15) . . ?
O1 S9 C21 102.37(16) . . ?
F1 C21 F3 107.9(3) . . ?
F1 C21 F2 107.9(3) . . ?
F3 C21 F2 107.7(3) . . ?
F1 C21 S9 111.0(2) . . ?
F3 C21 S9 111.5(2) . . ?
F2 C21 S9 110.8(3) . . ?
O6 S10 O4 116.05(14) . . ?
O6 S10 O5 115.40(14) . . ?
O4 S10 O5 113.10(13) . . ?
O6 S10 C22 103.82(15) . . ?
O4 S10 C22 103.51(15) . . ?
O5 S10 C22 102.65(15) . . ?
F4 C22 F5 107.9(3) . . ?
F4 C22 F6 107.8(3) . . ?
F5 C22 F6 107.3(3) . . ?
F4 C22 S10 111.8(2) . . ?
F5 C22 S10 111.5(2) . . ?
F6 C22 S10 110.4(2) . . ?
Cl1 C23 Cl2 110.9(2) . . ?
Cl1 C23 H23A 109.5 . . ?
Cl2 C23 H23A 109.5 . . ?
Cl1 C23 H23B 109.5 . . ?
Cl2 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.8(4) . . . . ?
C5 N1 C1 S1 -176.4(2) . . . . ?
Fe1 S1 C1 N1 -149.9(2) . . . . ?
Fe1 S1 C1 C2 33.2(3) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
S1 C1 C2 C3 176.9(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C1 N1 C5 C4 -1.5(5) . . . . ?
C3 C4 C5 N1 1.3(5) . . . . ?
C10 N2 C6 C7 0.1(5) . . . . ?
C10 N2 C6 S2 -179.0(3) . . . . ?
Fe1 S2 C6 N2 -135.7(2) . . . . ?
Fe1 S2 C6 C7 45.3(3) . . . . ?
N2 C6 C7 C8 -0.5(4) . . . . ?
S2 C6 C7 C8 178.6(2) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C6 N2 C10 C9 0.2(5) . . . . ?
C8 C9 C10 N2 -0.1(5) . . . . ?
C15 N3 C11 C12 -2.6(5) . . . . ?
C15 N3 C11 S3 174.2(3) . . . . ?
Fe1 S3 C11 N3 153.5(2) . . . . ?
Fe1 S3 C11 C12 -30.1(3) . . . . ?
N3 C11 C12 C13 0.4(4) . . . . ?
S3 C11 C12 C13 -176.0(3) . . . . ?
C11 C12 C13 C14 1.9(5) . . . . ?
C12 C13 C14 C15 -2.2(5) . . . . ?
C11 N3 C15 C14 2.3(5) . . . . ?
C13 C14 C15 N3 0.2(5) . . . . ?
C20 N4 C16 C17 0.7(5) . . . . ?
C20 N4 C16 S4 -178.3(3) . . . . ?
Fe1 S4 C16 N4 171.3(2) . . . . ?
Fe1 S4 C16 C17 -7.5(3) . . . . ?
N4 C16 C17 C18 -0.4(5) . . . . ?
S4 C16 C17 C18 178.4(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 N4 -0.2(5) . . . . ?
C16 N4 C20 C19 -0.3(5) . . . . ?
O2 S9 C21 F1 68.8(3) . . . . ?
O3 S9 C21 F1 -168.9(2) . . . . ?
O1 S9 C21 F1 -50.8(3) . . . . ?
O2 S9 C21 F3 -170.9(2) . . . . ?
O3 S9 C21 F3 -48.6(3) . . . . ?
O1 S9 C21 F3 69.5(3) . . . . ?
O2 S9 C21 F2 -51.0(3) . . . . ?
O3 S9 C21 F2 71.3(3) . . . . ?
O1 S9 C21 F2 -170.6(2) . . . . ?
O6 S10 C22 F4 176.8(2) . . . . ?
O4 S10 C22 F4 55.2(3) . . . . ?
O5 S10 C22 F4 -62.6(3) . . . . ?
O6 S10 C22 F5 56.0(3) . . . . ?
O4 S10 C22 F5 -65.6(3) . . . . ?
O5 S10 C22 F5 176.5(2) . . . . ?
O6 S10 C22 F6 -63.2(2) . . . . ?
O4 S10 C22 F6 175.2(2) . . . . ?
O5 S10 C22 F6 57.3(2) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.073

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ph221_0m_sq_sqd
_database_code_depnum_ccdc_archive 'CCDC 1552420'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Fe2 N4 S4'
_chemical_formula_weight         552.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   27.8033(10)
_cell_length_b                   27.8033(10)
_cell_length_c                   21.6926(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     14522.3(14)
_cell_formula_units_Z            18
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3801
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      19.27

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             5040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.168
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32398
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.263
_diffrn_reflns_theta_max         24.34
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.612
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.612
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.612
_reflns_number_total             3576
_reflns_number_gt                2884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.004 1944 449 ' '
2 0.333 0.667 0.061 1939 449 ' '
3 0.667 0.333 0.728 1939 450 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          1348
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²+58.7656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.35165(3) 0.01067(3) 0.36326(3) 0.0429(2) Uani 1 1 d . . . . .
Fe2 Fe 0.35155(3) -0.00308(3) 0.53025(3) 0.0418(2) Uani 1 1 d . . . . .
S3 S 0.37905(5) 0.07729(5) 0.44873(5) 0.0460(3) Uani 1 1 d . . . . .
S4 S 0.34073(5) -0.06558(5) 0.43153(5) 0.0482(3) Uani 1 1 d . . . . .
S1 S 0.28895(5) -0.05403(5) 0.27352(5) 0.0499(3) Uani 1 1 d . . . . .
N3 N 0.43880(14) 0.04831(14) 0.51510(15) 0.0392(9) Uani 1 1 d . . . . .
C15 C 0.44305(18) 0.08333(17) 0.46895(19) 0.0409(11) Uani 1 1 d . . . . .
C14 C 0.4933(2) 0.11806(19) 0.4415(2) 0.0525(13) Uani 1 1 d . . . . .
H14 H 0.4955 0.1412 0.4093 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4852(2) 0.0494(2) 0.5343(2) 0.0534(13) Uani 1 1 d . . . . .
H11 H 0.4824 0.0258 0.5661 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5360(2) 0.0835(2) 0.5093(2) 0.0622(14) Uani 1 1 d . . . . .
H12 H 0.5674 0.0833 0.5238 0.075 Uiso 1 1 calc R U . . .
C13 C 0.5399(2) 0.1183(2) 0.4620(2) 0.0659(15) Uani 1 1 d . . . . .
H13 H 0.5741 0.1420 0.4441 0.079 Uiso 1 1 calc R U . . .
N1 N 0.27053(16) 0.00015(16) 0.35858(17) 0.0505(10) Uani 1 1 d . . . . .
C1 C 0.2420(2) 0.0196(2) 0.3906(2) 0.0659(15) Uani 1 1 d . . . . .
H1 H 0.2581 0.0412 0.4255 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2469(2) -0.0314(2) 0.3082(2) 0.0514(13) Uani 1 1 d . . . . .
C4 C 0.1948(2) -0.0430(2) 0.2877(3) 0.0694(16) Uani 1 1 d . . . . .
H4 H 0.1794 -0.0642 0.2524 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1898(3) 0.0084(3) 0.3729(3) 0.0873(19) Uani 1 1 d . . . . .
H2 H 0.1707 0.0217 0.3960 0.105 Uiso 1 1 calc R U . . .
C3 C 0.1664(2) -0.0227(3) 0.3204(3) 0.0881(19) Uani 1 1 d . . . . .
H3 H 0.1316 -0.0299 0.3072 0.106 Uiso 1 1 calc R U . . .
N4 N 0.26819(15) -0.05897(15) 0.50086(16) 0.0446(9) Uani 1 1 d . . . . .
C20 C 0.27279(19) -0.08730(19) 0.4529(2) 0.0499(12) Uani 1 1 d . . . . .
C16 C 0.2175(2) -0.0719(2) 0.5218(2) 0.0572(14) Uani 1 1 d . . . . .
H16 H 0.2147 -0.0520 0.5547 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1698(2) -0.1138(3) 0.4958(3) 0.0775(17) Uani 1 1 d . . . . .
H17 H 0.1352 -0.1223 0.5111 0.093 Uiso 1 1 calc R U . . .
C19 C 0.2250(2) -0.1303(2) 0.4246(2) 0.0641(15) Uani 1 1 d . . . . .
H19 H 0.2282 -0.1495 0.3913 0.077 Uiso 1 1 calc R U . . .
C7 C 0.5132(2) 0.0288(2) 0.3055(2) 0.0554(14) Uani 1 1 d . . . . .
H7 H 0.5363 0.0141 0.3128 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4630(2) 0.0077(2) 0.33494(19) 0.0490(12) Uani 1 1 d . . . . .
H6 H 0.4525 -0.0213 0.3627 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5289(2) 0.0726(2) 0.2643(2) 0.0581(14) Uani 1 1 d . . . . .
H8 H 0.5630 0.0880 0.2443 0.070 Uiso 1 1 calc R U . . .
N2 N 0.42831(14) 0.02763(15) 0.32516(14) 0.0388(9) Uani 1 1 d . . . . .
S2 S 0.39430(5) 0.09114(5) 0.27477(5) 0.0408(3) Uani 1 1 d . . . . .
C10 C 0.44305(18) 0.06972(18) 0.28496(19) 0.0400(11) Uani 1 1 d . . . . .
C9 C 0.49369(19) 0.09276(19) 0.2537(2) 0.0517(13) Uani 1 1 d . . . . .
H9 H 0.5034 0.1216 0.2259 0.062 Uiso 1 1 calc R U . . .
C18 C 0.1738(2) -0.1434(2) 0.4464(3) 0.0795(18) Uani 1 1 d . . . . .
H18 H 0.1419 -0.1718 0.4283 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N2 2.108(3) . ?
Fe1 N1 2.127(4) . ?
Fe1 S3 2.4571(13) . ?
Fe1 S4 2.4770(13) . ?
Fe1 S1 2.6323(13) . ?
Fe1 S2 2.7285(13) . ?
Fe2 N3 2.137(3) . ?
Fe2 N4 2.143(4) . ?
Fe2 S2 2.4673(12) 6 ?
Fe2 S1 2.4752(13) 6 ?
Fe2 S3 2.6453(12) . ?
Fe2 S4 2.6783(13) . ?
S3 C15 1.757(4) . ?
S4 C20 1.734(5) . ?
S1 C5 1.749(5) . ?
S1 Fe2 2.4751(13) 8_544 ?
N3 C11 1.340(5) . ?
N3 C15 1.360(5) . ?
C15 C14 1.374(6) . ?
C14 C13 1.366(6) . ?
C14 H14 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 C1 1.355(6) . ?
N1 C5 1.349(6) . ?
C1 C2 1.376(7) . ?
C1 H1 0.9300 . ?
C5 C4 1.391(6) . ?
C4 C3 1.375(7) . ?
C4 H4 0.9300 . ?
C2 C3 1.382(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N4 C16 1.348(6) . ?
N4 C20 1.349(5) . ?
C20 C19 1.409(6) . ?
C16 C17 1.375(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(8) . ?
C17 H17 0.9300 . ?
C19 C18 1.364(7) . ?
C19 H19 0.9300 . ?
C7 C6 1.373(6) . ?
C7 C8 1.392(6) . ?
C7 H7 0.9300 . ?
C6 N2 1.347(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.370(6) . ?
C8 H8 0.9300 . ?
N2 C10 1.348(5) . ?
S2 C10 1.746(4) . ?
S2 Fe2 2.4673(12) 8_544 ?
C10 C9 1.396(6) . ?
C9 H9 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N1 153.66(13) . . ?
N2 Fe1 S3 103.27(9) . . ?
N1 Fe1 S3 92.72(12) . . ?
N2 Fe1 S4 95.93(10) . . ?
N1 Fe1 S4 104.07(10) . . ?
S3 Fe1 S4 93.05(4) . . ?
N2 Fe1 S1 96.49(9) . . ?
N1 Fe1 S1 64.93(11) . . ?
S3 Fe1 S1 157.36(5) . . ?
S4 Fe1 S1 95.82(4) . . ?
N2 Fe1 S2 64.18(10) . . ?
N1 Fe1 S2 94.32(10) . . ?
S3 Fe1 S2 93.95(4) . . ?
S4 Fe1 S2 159.96(4) . . ?
S1 Fe1 S2 84.71(4) . . ?
N3 Fe2 N4 153.33(14) . . ?
N3 Fe2 S2 93.63(10) . 6 ?
N4 Fe2 S2 100.39(9) . 6 ?
N3 Fe2 S1 107.46(10) . 6 ?
N4 Fe2 S1 94.19(11) . 6 ?
S2 Fe2 S1 93.92(4) 6 6 ?
N3 Fe2 S3 65.19(10) . . ?
N4 Fe2 S3 99.48(9) . . ?
S2 Fe2 S3 158.80(4) 6 . ?
S1 Fe2 S3 91.93(4) 6 . ?
N3 Fe2 S4 91.87(9) . . ?
N4 Fe2 S4 64.00(11) . . ?
S2 Fe2 S4 97.60(4) 6 . ?
S1 Fe2 S4 156.81(5) 6 . ?
S3 Fe2 S4 84.54(4) . . ?
C15 S3 Fe1 100.25(14) . . ?
C15 S3 Fe2 76.40(15) . . ?
Fe1 S3 Fe2 91.02(4) . . ?
C20 S4 Fe1 95.96(15) . . ?
C20 S4 Fe2 76.21(17) . . ?
Fe1 S4 Fe2 89.82(4) . . ?
C5 S1 Fe2 98.83(15) . 8_544 ?
C5 S1 Fe1 76.68(17) . . ?
Fe2 S1 Fe1 91.58(4) 8_544 . ?
C11 N3 C15 118.3(4) . . ?
C11 N3 Fe2 136.4(3) . . ?
C15 N3 Fe2 104.8(3) . . ?
N3 C15 C14 121.1(4) . . ?
N3 C15 S3 113.2(3) . . ?
C14 C15 S3 125.7(4) . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N3 C11 C12 123.0(4) . . ?
N3 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C13 118.3(5) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C1 N1 C5 118.9(4) . . ?
C1 N1 Fe1 135.5(4) . . ?
C5 N1 Fe1 105.4(3) . . ?
N1 C1 C2 121.9(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N1 C5 C4 121.4(5) . . ?
N1 C5 S1 112.8(4) . . ?
C4 C5 S1 125.8(4) . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C16 N4 C20 119.8(4) . . ?
C16 N4 Fe2 134.5(3) . . ?
C20 N4 Fe2 105.6(3) . . ?
N4 C20 C19 120.4(5) . . ?
N4 C20 S4 114.1(3) . . ?
C19 C20 S4 125.5(4) . . ?
N4 C16 C17 121.7(5) . . ?
N4 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 119.2(5) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C18 C19 C20 119.4(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C6 C7 C8 118.7(4) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N2 C6 C7 122.4(4) . . ?
N2 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C6 N2 C10 119.3(4) . . ?
C6 N2 Fe1 134.2(3) . . ?
C10 N2 Fe1 106.4(3) . . ?
C10 S2 Fe2 97.48(14) . 8_544 ?
C10 S2 Fe1 74.00(16) . . ?
Fe2 S2 Fe1 89.49(4) 8_544 . ?
N2 C10 C9 120.7(4) . . ?
N2 C10 S2 115.3(3) . . ?
C9 C10 S2 124.0(4) . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 S2 0.93 2.96 3.606(5) 127.5 18_545
C12 H12 S4 0.93 2.99 3.917(5) 172.1 10_656
C7 H7 S2 0.93 2.96 3.606(5) 127.5 18_545
C12 H12 S4 0.93 2.99 3.917(5) 172.1 10_656
C7 H7 S2 0.93 2.96 3.606(5) 127.5 18_545
C1 H1 S3 0.93 3.03 3.546(6) 116.4 .
C12 H12 S4 0.93 2.99 3.917(5) 172.1 10_656
C7 H7 S2 0.93 2.96 3.606(5) 127.5 18_545
C1 H1 S3 0.93 3.03 3.546(6) 116.4 .
C12 H12 S4 0.93 2.99 3.917(5) 172.1 10_656
C12 H12 S4 0.93 2.99 3.917(5) 172.1 10_656
C7 H7 S2 0.93 2.96 3.606(5) 127.5 18_545

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PH151116_a
_database_code_depnum_ccdc_archive 'CCDC 1552418'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl2 Fe N4 O8 S4'
_chemical_formula_weight         699.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.948(5)
_cell_length_b                   20.583(7)
_cell_length_c                   18.824(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.376(10)
_cell_angle_gamma                90
_cell_volume                     5830(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2238
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      24.7

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.037
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36742
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.677
_diffrn_reflns_theta_max         25.789
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5580
_reflns_number_gt                4283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+14.1857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5580
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   0.743
_refine_ls_restrained_S_all      0.743
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe2 Fe 1.0000 0.31256(2) 0.7500 0.04736(17) Uani 1 2 d S T P . .
Fe1 Fe 0.5000 0.31063(3) 0.7500 0.0619(2) Uani 1 2 d S T P . .
Cl2 Cl 0.62437(5) 0.58618(3) 0.58467(4) 0.05064(18) Uani 1 1 d . . . . .
S3 S 0.94535(6) 0.39286(3) 0.80991(5) 0.0595(2) Uani 1 1 d . . . . .
Cl1 Cl 0.62523(6) 0.07665(4) 0.55410(5) 0.0692(2) Uani 1 1 d . . . . .
S4 S 0.89629(6) 0.24028(3) 0.67413(5) 0.0662(2) Uani 1 1 d . . . . .
S2 S 0.61828(6) 0.37428(4) 0.74068(5) 0.0672(2) Uani 1 1 d . . . . .
S1 S 0.46711(7) 0.24744(4) 0.63979(5) 0.0740(3) Uani 1 1 d . . . . .
N3 N 0.85560(17) 0.40123(12) 0.90364(14) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.61889(17) 0.50134(12) 0.76140(15) 0.0511(6) Uani 1 1 d . . . . .
O6 O 0.69068(18) 0.60466(13) 0.55312(14) 0.0780(7) Uani 1 1 d . . . . .
O5 O 0.6455(2) 0.52371(11) 0.61865(15) 0.0825(8) Uani 1 1 d . . . . .
O7 O 0.6218(2) 0.63139(12) 0.64130(15) 0.0897(9) Uani 1 1 d . . . . .
N1 N 0.4470(2) 0.12001(14) 0.63770(19) 0.0663(8) Uani 1 1 d . . . . .
O8 O 0.54126(19) 0.58352(18) 0.52666(18) 0.1058(10) Uani 1 1 d . . . . .
C15 C 0.88882(18) 0.35957(13) 0.86512(16) 0.0462(6) Uani 1 1 d . . . . .
N4 N 0.7278(2) 0.25035(16) 0.59215(19) 0.0724(8) Uani 1 1 d . . . . .
C9 C 0.5961(2) 0.44420(14) 0.86042(16) 0.0546(7) Uani 1 1 d . . . . .
H9 H 0.5914 0.4046 0.8847 0.065 Uiso 1 1 calc R U . . .
C10 C 0.61100(19) 0.44270(14) 0.79142(16) 0.0501(6) Uani 1 1 d . . . . .
C8 C 0.5882(2) 0.50184(15) 0.89350(17) 0.0582(7) Uani 1 1 d . . . . .
H8 H 0.5773 0.5019 0.9401 0.070 Uiso 1 1 calc R U . . .
O4 O 0.5528(2) 0.12037(16) 0.5297(2) 0.1116(11) Uani 1 1 d . . . . .
C11 C 0.8085(2) 0.38387(15) 0.94871(18) 0.0556(7) Uani 1 1 d . . . . .
H11 H 0.7870 0.4160 0.9746 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5961(2) 0.56041(14) 0.85964(18) 0.0598(8) Uani 1 1 d . . . . .
H7 H 0.5903 0.6006 0.8824 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6121(2) 0.55877(14) 0.79301(18) 0.0577(7) Uani 1 1 d . . . . .
H6 H 0.6186 0.5981 0.7689 0.069 Uiso 1 1 calc R U . . .
C20 C 0.8030(2) 0.28384(14) 0.62466(17) 0.0549(7) Uani 1 1 d . . . . .
C14 C 0.8743(2) 0.29394(14) 0.87384(19) 0.0650(9) Uani 1 1 d . . . . .
H14 H 0.8974 0.2622 0.8487 0.078 Uiso 1 1 calc R U . . .
O3 O 0.6192(3) 0.03868(14) 0.61477(18) 0.1263(14) Uani 1 1 d . . . . .
C5 C 0.4241(2) 0.17643(15) 0.66247(18) 0.0598(8) Uani 1 1 d . . . . .
C12 C 0.7924(3) 0.32062(15) 0.9564(2) 0.0693(9) Uani 1 1 d . . . . .
H12 H 0.7585 0.3073 0.9868 0.083 Uiso 1 1 calc R U . . .
O2 O 0.6311(3) 0.03579(17) 0.4967(2) 0.1322(14) Uani 1 1 d . . . . .
C4 C 0.3675(2) 0.17111(19) 0.7049(2) 0.0709(9) Uani 1 1 d . . . . .
H4 H 0.3470 0.2094 0.7221 0.085 Uiso 1 1 calc R U . . .
C19 C 0.7981(3) 0.35088(17) 0.6145(2) 0.0796(11) Uani 1 1 d . . . . .
H19 H 0.8499 0.3767 0.6345 0.095 Uiso 1 1 calc R U . . .
C13 C 0.8264(3) 0.27525(16) 0.9189(2) 0.0766(11) Uani 1 1 d . . . . .
H13 H 0.8164 0.2303 0.9246 0.092 Uiso 1 1 calc R U . . .
C1 C 0.4223(3) 0.06062(17) 0.6538(3) 0.0828(12) Uani 1 1 d . . . . .
H1 H 0.4418 0.0227 0.6352 0.099 Uiso 1 1 calc R U . . .
C2 C 0.3694(3) 0.0556(2) 0.6969(3) 0.0899(13) Uani 1 1 d . . . . .
H2 H 0.3520 0.0141 0.7095 0.108 Uiso 1 1 calc R U . . .
C3 C 0.3411(3) 0.1117(2) 0.7223(2) 0.0847(11) Uani 1 1 d . . . . .
H3 H 0.3032 0.1090 0.7519 0.102 Uiso 1 1 calc R U . . .
O1 O 0.7033(2) 0.11431(18) 0.5817(3) 0.1596(19) Uani 1 1 d . . . . .
C17 C 0.6434(3) 0.3429(3) 0.5458(3) 0.0952(14) Uani 1 1 d . . . . .
H17 H 0.5881 0.3631 0.5202 0.114 Uiso 1 1 calc R U . . .
C16 C 0.6489(3) 0.2780(3) 0.5530(3) 0.0962(14) Uani 1 1 d . . . . .
H16 H 0.5980 0.2517 0.5308 0.115 Uiso 1 1 calc R U . . .
C18 C 0.7185(4) 0.3797(2) 0.5756(3) 0.0964(14) Uani 1 1 d . . . . .
H18 H 0.7155 0.4256 0.5694 0.116 Uiso 1 1 calc R U . . .
H2A H 0.627(2) 0.5016(15) 0.7230(18) 0.050(9) Uiso 1 1 d . . . . .
H1A H 0.477(2) 0.1220(15) 0.6151(17) 0.037(9) Uiso 1 1 d . . . . .
H3A H 0.869(2) 0.4343(15) 0.9044(17) 0.044(9) Uiso 1 1 d . . . . .
H4A H 0.736(3) 0.208(2) 0.599(3) 0.101(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe2 S3 2.3272(9) 2_756 ?
Fe2 S3 2.3272(9) . ?
Fe2 S4 2.3284(10) . ?
Fe2 S4 2.3285(10) 2_756 ?
Fe1 S2 2.3506(11) 2_656 ?
Fe1 S2 2.3507(11) . ?
Fe1 S1 2.3556(11) 2_656 ?
Fe1 S1 2.3556(11) . ?
Cl2 O8 1.411(3) . ?
Cl2 O6 1.426(2) . ?
Cl2 O7 1.426(2) . ?
Cl2 O5 1.426(2) . ?
S3 C15 1.727(3) . ?
Cl1 O2 1.396(3) . ?
Cl1 O1 1.411(4) . ?
Cl1 O3 1.413(3) . ?
Cl1 O4 1.416(3) . ?
S4 C20 1.722(3) . ?
S2 C10 1.727(3) . ?
S1 C5 1.728(3) . ?
N3 C15 1.340(3) . ?
N3 C11 1.355(4) . ?
N3 H3A 0.71(3) . ?
N2 C6 1.344(4) . ?
N2 C10 1.356(4) . ?
N2 H2A 0.77(3) . ?
N1 C5 1.347(4) . ?
N1 C1 1.350(5) . ?
N1 H1A 0.73(3) . ?
C15 C14 1.390(4) . ?
N4 C20 1.342(4) . ?
N4 C16 1.354(5) . ?
N4 H4A 0.89(5) . ?
C9 C8 1.365(4) . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C8 C7 1.389(4) . ?
C8 H8 0.9500 . ?
C11 C12 1.344(4) . ?
C11 H11 0.9500 . ?
C7 C6 1.361(5) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C20 C19 1.392(4) . ?
C14 C13 1.372(4) . ?
C14 H14 0.9500 . ?
C5 C4 1.393(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C4 C3 1.369(5) . ?
C4 H4 0.9500 . ?
C19 C18 1.371(6) . ?
C19 H19 0.9500 . ?
C13 H13 0.9500 . ?
C1 C2 1.355(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C17 C16 1.343(7) . ?
C17 C18 1.370(7) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S3 Fe2 S3 89.49(5) 2_756 . ?
S3 Fe2 S4 117.43(4) 2_756 . ?
S3 Fe2 S4 116.55(4) . . ?
S3 Fe2 S4 116.55(4) 2_756 2_756 ?
S3 Fe2 S4 117.43(4) . 2_756 ?
S4 Fe2 S4 100.57(5) . 2_756 ?
S2 Fe1 S2 112.25(5) 2_656 . ?
S2 Fe1 S1 101.05(4) 2_656 2_656 ?
S2 Fe1 S1 115.08(4) . 2_656 ?
S2 Fe1 S1 115.08(4) 2_656 . ?
S2 Fe1 S1 101.05(4) . . ?
S1 Fe1 S1 112.97(6) 2_656 . ?
O8 Cl2 O6 108.90(19) . . ?
O8 Cl2 O7 110.6(2) . . ?
O6 Cl2 O7 110.26(17) . . ?
O8 Cl2 O5 109.5(2) . . ?
O6 Cl2 O5 109.27(16) . . ?
O7 Cl2 O5 108.32(16) . . ?
C15 S3 Fe2 111.34(9) . . ?
O2 Cl1 O1 109.8(3) . . ?
O2 Cl1 O3 109.4(2) . . ?
O1 Cl1 O3 107.1(3) . . ?
O2 Cl1 O4 112.9(2) . . ?
O1 Cl1 O4 107.2(2) . . ?
O3 Cl1 O4 110.3(2) . . ?
C20 S4 Fe2 108.03(11) . . ?
C10 S2 Fe1 102.14(11) . . ?
C5 S1 Fe1 103.90(12) . . ?
C15 N3 C11 124.8(3) . . ?
C15 N3 H3A 117(3) . . ?
C11 N3 H3A 117(3) . . ?
C6 N2 C10 124.5(3) . . ?
C6 N2 H2A 118(2) . . ?
C10 N2 H2A 118(2) . . ?
C5 N1 C1 124.7(4) . . ?
C5 N1 H1A 117(3) . . ?
C1 N1 H1A 118(3) . . ?
N3 C15 C14 116.5(2) . . ?
N3 C15 S3 116.8(2) . . ?
C14 C15 S3 126.7(2) . . ?
C20 N4 C16 124.1(4) . . ?
C20 N4 H4A 112(3) . . ?
C16 N4 H4A 124(3) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N2 C10 C9 115.8(3) . . ?
N2 C10 S2 117.6(2) . . ?
C9 C10 S2 126.6(2) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C12 C11 N3 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
N3 C11 H11 120.4 . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N2 C6 C7 119.8(3) . . ?
N2 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N4 C20 C19 116.4(3) . . ?
N4 C20 S4 117.4(2) . . ?
C19 C20 S4 126.2(3) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N1 C5 C4 115.7(3) . . ?
N1 C5 S1 117.9(3) . . ?
C4 C5 S1 126.4(3) . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N1 C1 C2 119.4(4) . . ?
N1 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C16 C17 C18 119.3(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C16 N4 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
N4 C16 H16 120.3 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

